TWI434872B - A thermosetting resin composition, and a pre-absorbent body and a laminate using the same - Google Patents
A thermosetting resin composition, and a pre-absorbent body and a laminate using the same Download PDFInfo
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- TWI434872B TWI434872B TW96136368A TW96136368A TWI434872B TW I434872 B TWI434872 B TW I434872B TW 96136368 A TW96136368 A TW 96136368A TW 96136368 A TW96136368 A TW 96136368A TW I434872 B TWI434872 B TW I434872B
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- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/15—Heterocyclic compounds having oxygen in the ring
- C08K5/151—Heterocyclic compounds having oxygen in the ring having one oxygen atom in the ring
- C08K5/1535—Five-membered rings
- C08K5/1539—Cyclic anhydrides
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- H05K1/00—Printed circuits
- H05K1/02—Details
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- H05K1/0313—Organic insulating material
- H05K1/0353—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement
- H05K1/0373—Organic insulating material consisting of two or more materials, e.g. two or more polymers, polymer + filler, + reinforcement containing additives, e.g. fillers
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
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- C08G59/50—Amines
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Description
本發明係有關熱硬化性樹脂組成物及使用其之預漬體以及層合板,該熱硬化性樹脂組成物的金屬箔黏著性、耐熱性、耐濕性、難燃性、貼金屬耐熱性、介電特性(相對介電常數(relative dielectric constant)、介電損耗角正切)均可均衡取得,且毒性低,安全性、作業環境均良好,適用於電子零件等。
熱硬化性樹脂其特有之交聯構造展現高度耐熱性、尺寸穩定性,因此廣泛用於電子零件等被要求高度可靠性之領域,特別是貼銅層合板或層間絕緣材料中,近年來對於高密度化之要求,為了形成微細配線之高銅箔黏著性、或藉由鑽頭、穿孔進行開孔等加工時之加工性亦為必要。
又,近年來環境問題上,被要求無鉛焊接之電子零件的搭載及無鹵素之難燃化,因此務必比先行技術具更高的耐熱性及難燃性。進而,為了製品之安全性、作業環境之提昇,而期待僅以毒性低之成份所構成且不產生毒性氣體等之熱硬化性樹脂組成物。
雙順丁烯二醯亞胺化合物係具有良好的介電特性、難燃性、耐熱性之熱硬化性樹脂用之硬化劑,但公知之雙順丁烯二醯亞胺化合物不具與環氧樹脂之硬化反應性,因此直接用於環氧硬化系之熱硬化性樹脂時,有耐熱性不足之
問題點。亦即,雖揭示有關熱硬化性樹脂之相關事例,其使用未使用有機溶劑而藉由加熱混煉製造雙順丁烯二醯亞胺化合物與胺基苯酚之加成物(專利文獻1~2),惟雙順丁烯二醯亞胺化合物與胺基苯酚之加成物之收率低,以此作為貼銅層合板、層間絕緣材料使用後,其耐熱性、加工性等均不足。
又,熱硬化性樹脂之蜜胺樹脂、鳥糞胺化合物雖具有良好的黏著性、難燃性及耐熱性,對於有機溶劑之溶解性卻不足,若未大量使用毒性高之N,N-二甲基甲醯胺等含有氮原子之有機溶劑則不易製作熱硬化性樹脂組成物,且有保存穩定性不足之問題點。又,使用此等熱硬化性樹脂之貼銅層合板、層間絕緣材料,於製造電子零件等時,將有污染鍍敷液等各種藥液之問題。
為解決此等問題,已知有使用蜜胺樹脂或鳥糞胺化合物之熱硬化性樹脂相關之諸多事例(專利文獻3~7)。惟,此等係利用甲醛等醛類,使蜜胺樹脂、鳥糞胺化合物進行縮合之熱硬化性樹脂,雖對於有機溶劑之溶解性有所改善,惟,其熱分解溫度低、產生毒性分解氣體,而導致作業環境的惡化,且對於近來所要求之無鉛焊接之耐熱性、貼銅耐熱性均不足。又於微細之加工處理、配線形成中,銅箔黏著性、流動性、韌性均不足,電路圖型產生斷線、剝離,藉由鑽頭、穿孔之開孔等加工時出現龜裂等不良情況。
另外,揭示有羥甲基化鳥糞胺樹脂之相關事例(專利
文獻8),而此等仍與上述同樣地存在有耐熱性、黏著性、加工性等問題。
更揭示有熱硬化性樹脂之相關事例,其使用未使用有機溶劑所製造之雙順丁烯二醯亞胺化合物與胺基苯甲酸之加成物、苯并鳥糞胺甲醛縮合物等(專利文獻9),惟其熱分解溫度低,對於近年所要求之無鉛焊接之耐熱性、貼銅耐熱性均不足。
使用以環氧樹脂為硬化劑,且含有馬來酸酐之共聚樹脂之樹脂組成物或層合板之事例,揭示有使用苯乙烯與馬來酸酐所形成之共聚樹脂等之可撓性印刷電路板(專利文獻10)。另外揭示有一種環氧樹脂化合物,其含有由環氧樹脂、芳香族乙烯酯化合物及馬來酸酐得到之酸價為280以上之共聚樹脂、以及雙氰胺(專利文獻11)。更揭示有含有溴化之環氧樹脂、苯乙烯與馬來酸酐之共聚樹脂(環氧樹脂硬化劑)、苯乙烯系化合物及溶劑之預漬體、電用層合板材料(專利文獻12);含有環氧樹脂、芳香族乙烯酯化合物與馬來酸酐之共聚樹脂、苯酚化合物之預漬體、電氣用層合板材料(專利文獻13)、含有環氧樹脂、芳香族乙烯酯化合物與馬來酸酐之共聚樹脂、苯酚化合物及苯乙烯或苯乙烯低聚物之預漬體、電氣用層合板材料(專利文獻14)、含有環氧樹脂、羧酸酐型之環氧樹脂用交聯劑、烯丙基網孔形成化合物之樹脂組成物、層合板、印刷電路板(專利文獻15)等。
惟,此等伴隨圖型之精密化、信號之高頻化等,所要
求之介電特性、高耐熱性、高耐濕性及與銅箔之高度黏著性等性能均不足。
專利文獻1:特公昭63-34899號公報
專利文獻2:特開平6-32969號公報
專利文獻3:特公昭62-46584號公報
專利文獻4:特開平10-67942號公報
專利文獻5:特開2001-11672號公報
專利文獻6:特開平02-258820號公報
專利文獻7:特開平03-145476號公報
專利文獻8:特公昭62-61051號公報
專利文獻9:特公平6-8342號公報
專利文獻10:特公昭49-109476號公報
專利文獻11:特開平1-221413號公報
專利文獻12:特開平9-25349號公報
專利文獻13:特開平10-17685號公報
專利文獻14:特開平10-17686號公報
專利文獻15:特表平10-505376號公報
本發明之目的係鑑於現狀,而提供一種熱硬化性樹脂組成物及使用其之預漬體與層合板,該熱硬化性樹脂組成物的金屬箔黏著性、耐熱性、耐濕性、難燃性、貼金屬耐熱性、相對介電常數及介電損耗角正切均可均衡取得。
本發明者為達成上述目的,進行精密研討後結果發現
一種熱硬化性樹脂組成物,其含有藉由特定方法所製造之具有酸性取代基與不飽和順丁烯二醯亞胺基之硬化劑(以下,單稱為硬化劑)、6-取代鳥糞胺化合物含有特定單體單元之共聚樹脂、及環氧樹脂,可達成上述目的,適用於層合板用熱硬化性樹脂組成物。本發明基於此發現,進而完成本發明。
亦即,本發明係提供一種下述熱硬化性樹脂組成物、預漬體與層合板。
1.一種熱硬化性樹脂組成物,其特徵為含有:(A)具有酸性取代基與不飽和順丁烯二醯亞胺基(unsaturated maleimide group)的硬化劑,其為使(a-1)1分子中具有至少2個N-取代順丁烯二醯亞胺基之順丁烯二醯亞胺化合物與(a-2)下述一般式(1)所示具有酸性取代基之胺化合物,在有機溶劑中反應所製造;(B)下述一般式(2)所示6-取代鳥糞胺(6-substituted guanamine)化合物及/或雙氰胺(dicyandiamide);(C)含有(c-1)下述一般式(3)所示單體單元與(c-2)下述一般式(4)所示單體單元的共聚樹脂;以及(D)1分子中具有至少2個環氧基之環氧樹脂。
2.如上述1之熱硬化性樹脂組成物,其中,(A)硬化劑包含下述一般式(5)或下述一般式(6)所示化合物。
3.一種預漬體,其係將上述1或2之熱硬化性樹脂組成物,浸漬(impregnating)或塗佈(coating)於基材後,進行B階段化所得到之預漬體。
4.一種層合板,其係將上述3之預漬體予以層合成形得到之層合板。
5.如上述4的層合板,其中,在預漬體之至少一方使金屬箔重疊後,進行加熱加壓成形而得到貼有金屬箔之層合板。
本發明之熱硬化性樹脂組成物其金屬箔黏著性、耐熱性、耐濕性、難燃性、貼金屬耐熱性、相對介電常數及介電損耗角正切均可均衡取得,且其毒性低、安全性及作業環境亦良好。
因此,藉由本發明,可提供利用該熱硬化性樹脂組成物而具有良好性能之預漬體、層合板等。
以下,針對本發明進行詳細說明。
首先,本發明之熱硬化性樹脂組成物之(A)成份之硬化劑,係使(a-1)1分子中具有至少2個N-取代順丁烯二醯亞胺基之順丁烯二醯亞胺組成物與(a-2)下述一般式(1)所示具有酸性取代基之胺化合物,在有機溶劑中反應所製造之具有酸性取代基與不飽和順丁烯二醯亞胺基之硬化劑。
作為(a-1)1分子中具有至少2個N-取代順丁烯二醯亞胺基之順丁烯二醯亞胺化合物,例如:雙(4-順丁烯二醯亞胺苯基)甲烷、聚(順丁烯二醯亞胺苯基)甲烷、雙(4-順丁烯二醯亞胺苯基)醚、雙(4-順丁烯二醯亞胺苯基)碸、3,3-二甲基-5,5-二乙基-4,4-二苯基甲烷雙順丁烯二醯亞胺、4-甲基-1,3-伸苯基雙順丁烯二醯亞胺、m-伸苯基雙順丁烯二醯亞胺、2,2-雙[4-(4-順丁烯二醯亞胺苯氧基)苯基]丙烷等例,此等中以反應率高並可更高耐熱性化之雙(4-順丁烯二醯亞胺苯基)甲烷、m-伸苯基雙順丁烯二醯亞胺及
雙(4-順丁烯二醯亞胺苯基)碸為較佳;由價廉之觀點視之,以m-伸苯基雙順丁烯二醯亞胺及雙(4-順丁烯二醯亞胺苯基)甲烷為更佳;由對於溶劑之溶解性的觀點視之,雙(4-順丁烯二醯亞胺苯基)甲烷特別理想。
作為(a-2)一般式(1)所示之胺化合物,例如:m-胺酚、p-胺酚、o-胺酚、p-胺基苯甲酸、m-胺基苯甲酸、o-胺基苯甲酸、o-胺基苯磺酸、m-胺基苯磺酸、p-胺基苯磺酸、3,5-二羥基苯胺、3,5-二羧基苯胺等例,此等中,由溶解性、合成之收率的觀點視之,以m-胺酚、p-胺酚、p-胺基苯甲酸、m-胺基苯甲酸及3,5-二羥基苯胺為較佳;由耐熱性之觀點視之,以m-胺酚及p-胺酚更佳;由低毒性之觀點視之,m-胺酚特別理想。
(a-1)順丁烯二醯亞胺化合物與(a-2)胺化合物之使用量比,(a-1)順丁烯二醯亞胺化合物之順丁烯二醯亞胺基當量與(a-2)胺化合物之-NH2基換算之當量的當量比為以下之式:1.0≦(順丁烯二醯亞胺基當量)/(-NH2基換算之當量)≦10.0所示之範圍為宜,該當量比更佳為2.0~10.0之範圍。該當量比作成上述範圍內後,將不會引起對於溶劑之溶解性不足、凝膠化、熱硬化性樹脂之耐熱性的降低。
該反應所使用之有機溶劑並未特別限定,一般如:乙醇、丙醇、丁醇、甲基溶纖劑、丁基溶纖劑、丙二醇單甲
醚等之醇系溶劑、丙酮、丁酮、甲基異丁酮、環己酮等酮系溶劑、四氫呋喃等醚系溶劑、甲苯、二甲苯、均三甲苯等之芳香族系溶劑、二甲基甲醯胺、二甲基乙醯胺、N-甲基吡咯烷酮等之含氮溶劑、二甲亞碸等之含硫溶劑等例,可單獨使用1種或混合2種以上使用。
此等有機溶劑中,由其溶解性之觀點視之,以環己酮、丙二醇單甲醚及甲基溶纖劑為較佳,由其低毒性之觀點視之,以環己酮、丙二醇單甲醚為更佳,又以丙二醇單甲醚特別理想,其揮發性高,於製造預漬體時,不易殘留為殘餘溶劑。
有機溶劑之使用量,以(a-1)胺化合物與(a-2)順丁烯二醯亞胺化合物之總和每100質量份計,較佳為10~1000質量份,更佳為100~500質量份,特佳為200~500質量份。
反應溫度以50~200℃為宜,更佳為100~160℃。反應時間以0.1小時~10小時為宜,更佳為1~8小時。
該反應,可於必要時任意使用反應觸媒。反應觸媒並未特別限定,例如三乙胺、吡啶、三丁胺等之胺類,甲基咪唑、苯基咪唑等之咪唑類,三苯膦等之磷系觸媒等例,可單獨使用1種,或混合2種以上使用。
藉由此反應,例如使用雙(4-順丁烯二醯亞胺)化合物作為(a-1)順丁烯二醯亞胺化合物,與(a-2)胺化合物進行反應後,合成具有下述一般式(5)或一般式(6)所示之酸性取代基與不飽和順丁烯二醯亞胺基之硬化劑。
本發明之熱硬化性樹脂組成物之(B)成份為下述一般式(2)所示之6-取代鳥糞胺化合物及/或雙氰胺。作為一般式(2)所示之6-取代鳥糞胺化合物,例如:稱為苯并鳥糞胺之2,4-二胺基-6-苯基-s-三嗪、稱為乙醯鳥糞胺之2,4-二胺基-6-甲基-s-三嗪、2,4-二胺基-6-乙烯基-s-三嗪等例,其中又以反應之反應率高並可更高耐熱性化之苯并鳥糞胺及2,4-二胺基-6-乙烯基-s-三嗪為較佳,由低毒性且價廉之觀點視之,苯并鳥糞胺特別理想。雙氰胺係廣泛適用於工業用,價廉,同時具有良好的黏著性、耐熱性、硬化性。
本發明之熱硬化性樹脂組成物之(C)成份為含有(c-1)下述一般式(3)所示之單體單元及(c-2)下述一般式(4)所示之單體單元之共聚樹脂。
(c-1)一般式(3)所示之單體單元係由例如:苯乙烯、1-甲基苯乙烯、乙烯甲苯、二甲基苯乙烯、氯苯乙烯、溴苯乙烯等之苯乙烯化合物、乙烯、丙烯、異丁烯等之乙烯基化合物所得,必要時亦可混合2種以上之單體使用。
又,(c-2)一般式(4)所示之單體單元係由馬來酸酐所得。
(C)成份之共聚樹脂中,除上述之單體單元以外,更可含有各種可聚合之單體單元,作為可得到此等各種單體單元(c-3)之單體,例如:N-苯基順丁烯二醯亞胺、N-羥苯基順丁烯二醯亞胺、N-羧基苯基順丁烯二醯亞胺、N-環己基順丁烯二醯亞胺等之順丁烯二醯亞胺化合物、甲基丙
烯酸甲酯、丙烯酸甲酯等之具有甲基丙烯醯基或丙烯醯基之化合物等例,由介電特性、難燃性之觀點視之,以順丁烯二醯胺化合物為較佳,由耐濕耐熱性、黏著性之觀點視之,以N-苯基順丁烯二醯亞胺及N-羥基苯基順丁烯二醯亞胺為更佳。
將(C)成份之共聚樹脂中(c-1)之單體單元數設為m,(c-2)之單體單元數設為n,(c-3)之可共聚成份之單體單元數設為r時,(C)成份之共聚樹脂中單體比率(m/n)若考量介電特性、玻璃轉移溫度、耐濕耐熱性、黏著性之均衡,以0.8~19.0為宜,更佳為1.0~6.0。又,含有(c-3)之單體單元時之單體比率[m/(n+r)]若考量介電特性、玻璃轉移溫度、耐濕耐熱性、黏著性之均衡,以0.1~9.0為宜,更佳為1.0~6.0。
另外,(C)成份之共聚樹脂之重量平均分子量若考慮耐熱性、機械強度與成形加工性之均衡,以1,000~200,000為宜。又,重量平均分子量係使用四氫呋喃為洗提液藉由GPC進行測定,經由標準聚苯乙烯檢量線所換算之值。
本發明之熱硬化性樹脂組成物之(D)成份只要是1分子中具有2個以上環氧基之環氧樹脂即可,並未特別受限,例如:雙酚A系、雙酚F系、聯苯系、酚醛清漆系、多官能酚系、萘系、脂環式系及醇系等之縮水甘油醚、縮水甘油胺系以及縮水甘油酯系等例,可使用1種或混合2種以上。
此等中由介電特性、耐熱性、耐濕性及金屬箔黏著性
之觀點視之,以雙酚F型環氧樹脂、二環戊二烯型環氧樹脂、含萘環之環氧樹脂、聯苯型環氧樹脂、聯苯芳烷基型環氧樹脂、苯酚酚醛清漆型環氧樹脂及甲酚酚醛清漆型環氧樹脂較佳,由介電特性、高玻璃轉移溫度之觀點視之,以二環戊二烯型環氧樹脂、聯苯芳烷基型環氧樹脂、聯苯型環氧樹脂及苯酚酚醛清漆型環氧樹脂為更佳,由耐濕耐熱性之觀點視之,特別以苯酚酚醛清漆型環氧樹脂及二環戊二烯型環氧樹脂為佳。
本發明熱硬化性樹脂組成物中亦可併用環氧樹脂之硬化劑、硬化促進劑。作為環氧樹脂之硬化劑例如:馬來酸酐、馬來酸酐共聚物等酸酐、雙氰胺等之胺化合物、苯酚酚醛清漆、甲酚酚醛清漆等之苯酚化合物等例。此等中耐熱性良好之苯酚酚醛清漆、甲酚酚醛清漆等之苯酚化合物較佳,由難燃性、黏著性之提昇面而言,特別以甲酚酚醛清漆型苯酚樹脂為佳。
又,作為環氧樹脂的硬化促進劑之例,如:咪唑類及其衍生物、三級胺類及四級銨鹽等例。
本發明之熱硬化性樹脂組成物中各成份之含量,以(A)成份之具有酸性取代基與不飽和順丁烯二醯亞胺基之硬化劑之固形成份換算之質量與(B)~(D)成份之質量的總和100質量份中之質量而言,為如下者較佳。
(A)成份以1~95質量份為宜,更佳為20~95質量份,特別以20~90質量份為佳。(A)成份之含量為1質量份以上後,可提昇難燃性、黏著性、流動性,又,95質量份
以下後,將不會降低耐熱性。
(B)成份以1~95質量份為宜,20~95質量份為更佳,20~90質量份特別理想。(B)成份之含量為1質量份以上後,可提昇難燃性、黏著性、介電特性,又,95質量份以下將不會降低耐熱性。
(C)成份以1~50質量份為宜,較佳為1~30質量份,特別以1~20質量份為佳。當(C)成份之含量為1質量份以上則可提昇溶解性、介電特性,又,50質量份以下則不會降低難燃性。
(D)成份以1~95質量份宜,更佳為20~95質量份,特別以20~90質量份為佳。(D)成份之含量為1質量份以上後,可提昇難燃性、黏著性、耐熱性,又,95質量份以下,將不會降低介電特性。
本發明之熱硬化性樹脂中,作為(E)成份,可任意含有無機填充劑。作為無機填充劑例如:二氧化矽、雲母、滑石、玻璃之短纖維或微粉末及中空玻璃、三氧化銻、碳酸鈣、石英粉末、氫氧化鋁、氫氧化鎂等例,此等中由介電特性、耐熱性、難燃性之觀點視之,以二氧化矽、氫氧化鋁及氫氧化鎂為較佳,另外由價廉之觀點視之,更以二氧化矽及氫氧化鋁為佳。
(E)成份之含量,相對於(A)成份之硬化劑固形成份換算之質量與(B)~(D)成份之質量的總和100質量份,較佳為0~300質量份,更佳為20~200質量份,特別以20~150質量份為佳。當(E)成份之含量為300質量份以下則不會
降低成形性、黏著性。
本發明之熱硬化性樹脂組成物,更於不損及作為樹脂組成物之熱硬化性樹脂的性質下,可任意含有公知的熱塑性樹脂、彈性體、難燃劑、有機填充劑等。
作為熱塑性樹脂之例,如:聚四氟乙烯、聚乙烯、聚丙烯、聚苯乙烯、聚苯醚樹脂、苯氧基樹脂、聚碳酸酯樹脂、聚酯樹脂、聚醯胺樹脂、聚醯亞胺樹脂、二甲苯樹脂、石油樹脂、聚矽氧樹脂等例。
作為彈性體之例,如:聚丁二烯、聚丙烯腈、環氧改性聚丁二烯、馬來酸酐改性聚丁二烯、苯酚改性聚丁二烯、羧基改性聚丙烯腈等例。
作為難燃劑之例,如:含有溴、氯之含鹵素系難燃劑、磷酸三苯酯、磷酸三甲苯酯、參二氯丙基磷酸酯、偶磷氮(phosphazene)、紅磷等磷系難燃劑、三氧化銻、氫氧化鋁、氫氧化鎂等之無機物之難燃劑等例。此等難燃劑中,由環境面視之,以非鹵素系難燃劑之磷系難燃劑、無機物之難燃劑等為較佳。又,由價格較便宜且同時具有難燃性、耐熱性等其他特性之觀點視之,磷系難燃劑與氫氧化鋁等之無機物難燃劑合併使用特別理想。
作為有機填充劑之例,如:矽氧樹脂粉、聚四氟乙烯、聚乙烯、聚丙烯、聚苯乙烯、聚苯醚等有機物粉末等例。
又,作為本發明之熱硬化性樹脂組成物中之稀釋溶劑,可任意使用有機溶劑。該有機溶劑並未特別限定,例如
:丙酮、丁酮、甲基異丁酮、環己酮等之酮系溶劑、甲基溶纖劑等之醇系溶劑、四氫呋喃等之醚系溶劑、甲苯、二甲苯、均三甲苯等之芳香族系溶劑等例,可使用1種或混合2種以上使用。
對於該熱硬化性樹脂組成物更可任意含有紫外線吸收劑、抗氧化劑、光聚合引發劑、螢光增白劑及提昇密合性劑等,未特別限定,例如:苯并三唑系等之紫外線吸收劑、受阻酚系或苯乙烯化酚等之抗氧化劑、二苯甲酮類、苄基縮酮類、噻噸酮系等光聚合引發劑、芪衍生物等螢光增白劑、脲矽烷等尿素化合物、矽烷偶合劑等提昇密合性劑等例。
本發明之預漬體係使本發明之熱硬化性樹脂組成物浸漬或塗佈於基材後,進行B階段化所形成。亦即,本發明之熱硬化性樹脂組成物浸漬或塗佈於基材後,藉由加熱使其半硬化(B階段化)後製造本發明之預漬體。以下,針對本發明之預漬體進行詳述。
本發明預漬體所使用之基材,可使用於各種電絕緣材料用層合板所使用之公知者。作為該材質之例,如:E玻璃、D玻璃、S玻璃、及Q玻璃等無機物之纖維、聚醯亞胺、聚酯及聚四氟乙烯等之有機物之纖維及其混合物等例。此等基材具有例如:織布、不織布、粗紗、切股氈以及表面氈等形狀,材質及形狀係選自目的成形物之用途、性能,依需求可單獨或組合2種以上之材質及形狀。
基材之厚度並未特別限定,例如可使用約0.03~0.5mm
者,由其耐熱性、耐濕性、加工性面視之,以矽烷偶合劑等進行表面處理者、或機械性進行開纖處理者為理想。對於該基材之樹脂組成物的附著量,以乾燥後之預漬體之樹脂含量百分比計為20~90質量%,浸漬或塗佈於基材後,通常於100~200℃之溫度下進行1~30分鐘之加熱乾燥,使其半硬化(B階段化)後,可得到本發明之預漬體。
本發明之層合板係使本發明預漬體經層合成形取得。亦即,將本發明預漬體,例如:將1~20片重疊且於其單面或雙面上配置銅及鋁等金屬箔此一構造,進行層合成形者。成形條件可適用例如:電絕緣材料用層合板及多層板之方法,例如:多段加壓,多段真空加壓,連續成形,高壓鍋成形機等,於溫度100~250℃,壓力0.2~10MPa,加熱時間0.1~5小時之範圍下可成形。又,組合本發明之預漬體與內層用配線板,層合成形後,亦可製造多層板。
接著,藉由下述實施例進行本發明更詳細的說明,惟本發明並未受限於此等實施例。
另外,以下實施例所得之貼銅層合板係依以下方法進行測定、評定性能。
使貼銅層合板浸漬於銅蝕刻液後,留1cm寬之帶部份,製作去除銅箔之評定基板,使用自動記錄試驗機[島
津製作所(股份)製AG-100C],測定帶部份之剝離強度。
使貼銅層合板浸漬於銅蝕刻液後,製作去除銅箔之5mm見方之評定基板,利用TMA試驗裝置[DuPont(股份)製TMA2940],藉由觀測評定基板之熱膨脹特性進行評定。
使貼銅層合板浸漬於銅蝕刻液後,製作去除銅箔之5cm見方之評定基板,利用壓力鍋試驗裝置[平山製作所(股份)製],於121℃,0.2MPa之條件下放置4小時,再於溫度288℃之焊浴中浸漬20秒後,藉由觀測評定基板之外觀,進行評定焊接耐熱性。
由貼銅層合板製作5mm見方之評定基板,利用TMA試驗裝置[DuPont(股份)製TMA2940],測定於288℃,其所評定基板出現膨脹為止之時間,進行評定。
使貼銅層合板浸漬於銅蝕刻液後,製作去除銅箔之評定基板,利用壓力鍋試驗裝置[平山製作所(股份)製],於121℃,0.2MPa之條件下放置4小時後,測定評定基板之
吸水率。
使貼銅層合板浸漬於銅蝕刻液後由去除銅箔之評定基板,製成切取長度127mm、寬12.7mm之評定基板,依UL94之試驗法(V法)為基準進行評定。
將所得之貼銅層合板浸漬於銅蝕刻液後製作去除銅箔之評定基板,利用相對介電常數測定裝置(Hewllet Packerd公司製、HP4291B),測定於頻率1GHz之相對介電常數及介電損耗角正切。
於附有溫度計、攪拌裝置、迴流冷卻管並附有水份定量器且可加熱及冷卻之容積2l的反應容器中,置入雙(4-順丁烯二醯亞胺苯基)甲烷:358.0g、與m-胺酚:54.5g、及丙二醇單甲醚:412.5g,進行迴流,同時反應5小時後,得到硬化劑(A-1)之溶液。
於附有溫度計、攪拌裝置、迴流冷卻管並附水份定量器且可加熱及冷卻之容積2l的反應容器中,置入雙(4-順丁烯二醯亞胺苯基)甲烷:358.0g、與p-胺酚:54.5g、及
丙二醇單甲醚:412.5g,進行迴流,同時反應5小時後,得到硬化劑(A-2)之溶液。
於附有溫度計、攪拌裝置、迴流冷卻管並附水份定量器且可加熱及冷卻之容積2l的反應容器中,置入雙(4-順丁烯二醯亞胺苯基)甲烷:358.0g、與p-胺基苯甲酸:68.5g、及N,N-二甲基乙醯胺:426.5g,於140℃反應5小時後,得到硬化劑(A-3)之溶液。
於附有溫度計、攪拌裝置、迴流冷卻管並附水份定量器且可加熱及冷卻之容積1l的反應容器中,置入m-伸苯基雙順丁烯二醯亞胺:268.0g、與m-胺酚:54.5g、及N,N-二甲基乙醯胺:322.5g,於140℃反應5小時後,得到硬化劑(A-4)之溶液。
於附有溫度計、攪拌裝置、迴流冷卻管並附有水份定量器且可加熱及冷卻之容積2l的反應容器中,置入雙(4-順丁烯二醯亞胺苯基)碸:408.0g、與p-胺酚:54.5g、及N,N-二甲基乙醯胺:462.5g,於100℃反應2小時後,得到硬化劑(A-5)之溶液。
於附有溫度計、攪拌裝置、迴流冷卻管並附水份定量器且可加熱及冷卻之容積2l的反應容器中,置入雙(4-順丁烯二醯亞胺苯基)醚:360.0g、與p-胺酚:54.5g、及N,N-二甲基乙醯胺:414.5g,於100℃反應2小時後,得到硬化劑(A-6)之溶液。
於附有溫度計、攪拌裝置、迴流冷卻管並附水份定量器且可加熱及冷卻之容積2l的反應容器中,置入2,2’-雙[4-(4-順丁烯二醯亞胺苯氧基)苯基]丙烷:570.0g、與p-胺酚:54.5g、及丙二醇單甲醚:624.5g,於120℃反應2小時後,得到硬化劑(A-7)之溶液。
於附有溫度計、攪拌裝置、迴流冷卻管並附水份定量器且可加熱及冷卻之容積2l的反應容器中,置入4-甲基-1,3-伸苯基雙順丁烯二醯亞胺:282.0g、與p-胺酚:54.5g、及丙二醇單甲醚:336.5g,於120℃反應2小時後,得到硬化劑(A-8)之溶液。
於附有溫度計、攪拌裝置、迴流冷卻管並附水份定量器且可加熱及冷卻之容積2l的反應容器中,置入苯乙烯
(m)與馬來酸酐(n)之共聚樹脂(Elf Atochem公司製、商品名EF-40、單體比率(m/n)=4.0、重量平均分子量:10,000):514.0g、及環己酮:462.6g、甲苯:51.4g,昇溫至70℃,均勻溶解後,以少量逐滴加入苯胺:46.5g。再昇溫至迴流溫度,去除所產生之縮合水,同時反應5小時後,得到由苯乙烯與馬來酸酐及N-苯基順丁烯二醯亞胺所形成之共聚樹脂之溶液(C-1)。(C-1)之苯乙烯(m)與馬來酸酐(n)及N-苯基順丁烯二醯亞胺(r)之單體比率為m/(n+r)=4.0,重量平均分子量為11,000。
於附有溫度計、攪拌裝置、迴流冷卻管並附水份定量器且可加熱及冷卻之容積1l的反應容器中,置入異丁烯(m)與馬來酸酐(n)之共聚樹脂(Kuraray公司製、商品名Isobam 600、m/n=1.0、重量平均分子量:6,000):154.0g、及N,N-二甲基乙醯胺:308.0g、甲苯:30.8g,昇溫至70℃,均勻溶解後,以少量方式漸漸加入p-胺酚:54.5g。再昇溫至迴流溫度,去除所產生之縮合水,同時反應5小時後,得到異丁烯與馬來酸酐及N-羥苯基順丁烯二醯亞胺所形成之共聚樹脂之溶液(C-2)。(C-2)之異丁烯(m)與馬來酸酐(n)及p-羥苯基順丁烯二醯亞胺(r)之單體比率為m/(n+r)=1.0、重量平均分子量為7,000。
參考專利文獻1之實施例,於附有蒸氣加熱裝置之容積1l之捏合器中置入雙(4-順丁烯二醯亞胺苯基)甲烷:358.0g與m-胺酚:54.5g,於135~140℃下進行15分鐘加熱混煉後,冷卻,粉碎之後,得到硬化劑(A-9)之粉末。
參考專利文獻9之實施例,於附有蒸氣加熱裝置之容積1l之捏合器中,置入雙(4-順丁烯二醯亞胺苯基)甲烷:358.0g與m-胺基苯甲酸:68.5g,於135~140℃下進行15分鐘加熱混煉後,冷卻,粉碎之後,得到硬化劑(A-10)之粉末。
作為(A)成份之具有酸性取代基與不飽和順丁烯二醯亞胺基之硬化劑,是使用上述之製造例1~8所得之硬化劑(A-1~8)或比較製造例所得之硬化劑(A-9、10);作為(B)成份之6-取代鳥糞胺化合物,是使用苯并鳥糞胺[日本觸媒(股份)製]或雙氰胺[關東化學(股份)製];作為(C)成份之共聚樹脂是使用上述之製造例9~10所得之共聚樹脂(C-1、2)、苯乙烯與馬來酸酐之共聚樹脂(C-3:Elf Atochem公司製、商品名EF-40、m/n=4.0、重量平均分子量:10,000)或異丁烯與馬來酸酐之共聚樹脂(C-4:Kuraray公司製、商品名Isobam 600、m/n=1.0、重量平均分子量:6,000);作為(D)成份之環氧樹脂是使用苯酚酚醛清漆型環氧樹脂[D-
1:大日本油墨化學工業(股份)製、商品名:Epicron N-770]或二環戊二烯型環氧樹脂[D-2:大日本油墨化學工業(股份)製、商品名:HP-7200H]、環氧硬化劑者使用甲酚酚醛清漆型苯酚樹脂[大日本油墨化學工業(股份)製、商品名KA-1165]、作為(E)成份之無機填充劑,使用粉碎二氧化矽[E-1:福島窯業(股份)製、商品名:F05-30、平均粒徑10μm]及氫氧化鋁[E-2:昭和電工(股份)製、商品名:HD-360、平均粒徑3μm]、又,於稀釋溶劑中使用丁酮,以第1表~第3表所示之調配比例(質量份)進行混合後,得到70質量%樹脂份之均勻清漆。
接著,將所得之清漆浸漬於厚度0.2mm之E玻璃布後,於160℃進行10分鐘加熱乾燥,得到樹脂含量為55質量%之預漬體。將此預漬體4片重疊,將18μm之電解銅箔配置於上下,於壓力2.45MPa,溫度185℃進行加壓90分鐘,得到貼銅層合板。
利用所得之貼銅層合板,針對銅箔黏著性(銅箔剝離強度)、玻璃轉移溫度(Tg)、焊接耐熱性(T-288)、吸濕性(吸水率)、難燃性、相對介電常數(1GHz)及介電損耗角正切(1GHz),依上述方法進行測定、評定。評定結果示於第1表~第6表。
另外,比較例5及6之熱硬化性樹脂無法得到均勻溶解之清漆,未能製成預漬體。
由第1表~第4表證明,於本發明之實施例中其銅箔黏著性(銅箔剝離強度)、玻璃轉移溫度(Tg)、焊接耐熱性(T-288)、吸濕性(吸水率)、難燃性、相對介電常數(1GHz)及介電損耗角正切(1GHz)均可均衡取得。
反之,由第5表及第6表顯示,比較例無法製作預漬體,又,銅箔黏著性、玻璃轉移溫度、焊接耐熱性、吸濕性、難燃劑、相對介電常數及介電損耗角正切無法均衡取得,其中數個特性為不良。
本發明之熱硬化性樹脂組成物浸漬或塗佈於基材後所得預漬體、及將該預清體經由層合成形所製造之層合板,其銅箔黏著性、玻璃轉移溫度、焊接耐熱性、吸濕性、難燃劑、相對介電常數、介電損耗角正切均可均衡取得,適用於電子機器用印刷電路板。
Claims (5)
- 一種熱硬化性樹脂組成物,其特徵為含有:(A)具有酸性取代基與不飽和順丁烯二醯亞胺基的硬化劑,其為使(a-1)1分子中具有至少2個N-取代順丁烯二醯亞胺基之順丁烯二醯亞胺化合物與(a-2)下述一般式(1)所示具有酸性取代基之胺化合物,在有機溶劑中反應所製造;(B)下述一般式(2)所示6-取代鳥糞胺化合物及/或雙氰胺;(C)共聚樹脂,其含有(c-1)下述一般式(3)所示單體單元與(c-2)下述一般式(4)所示單體單元;以及(D)1分子中具有至少2個環氧基之環氧樹脂,
- 如申請專利範圍第1項之熱硬化性樹脂組成物,其中(A)硬化劑包含下述一般式(5)或下述一般式(6)所示化合 物,
- 一種預漬體,其特徵為將如申請專利範圍第1或2項之熱硬化性樹脂組成物,浸漬或塗覆於基材後,進行B階段化所得之預漬體。
- 一種層合板,其特徵為將如申請專利範圍第3項之預漬體予以層合成形得到之層合板。
- 如申請專利範圍第4項之層合板,其係在預漬體之至少一方使金屬箔重疊後,進行加熱加壓成形所得之貼有金屬箔之層合板。
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- 2007-09-10 KR KR1020097006405A patent/KR101398731B1/ko active IP Right Grant
- 2007-09-10 SG SG2011088424A patent/SG177151A1/en unknown
- 2007-09-28 TW TW96136368A patent/TWI434872B/zh active
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SG177151A1 (en) | 2012-01-30 |
CN102558505A (zh) | 2012-07-11 |
US9603244B2 (en) | 2017-03-21 |
TW200837094A (en) | 2008-09-16 |
US20170156207A1 (en) | 2017-06-01 |
KR20090074171A (ko) | 2009-07-06 |
CN101522752B (zh) | 2012-01-25 |
CN101522752A (zh) | 2009-09-02 |
WO2008041453A1 (fr) | 2008-04-10 |
KR101398731B1 (ko) | 2014-05-27 |
HK1131176A1 (en) | 2010-01-15 |
US20100143728A1 (en) | 2010-06-10 |
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